1. The Oregon Trail

It has been nearly 40 years of watching our friends and family die from dysentery, yet we keep coming back to The Oregon Trail. What started as an educational game to teach school kids about 19th century pioneering life, The Oregon Trail morphed into a piece of pop culture history. Who has not tried to caulk their wagon and float it across the Columbia River only to watch it sink like a stone? Who can’t remember being overjoyed at the sight of an approaching Fort Walla Walla during that perilous cross-country journey?

The unintentional comedy and popularity of The Oregon Trail helped to spur on the development of several spin-off pioneer games, such as The Yukon Trail and The Amazon Trail. Even today, new versions of the seminal 1971 classic are still popping up on all sorts of platforms, from the Nintendo DSi to the Apple iPhone. With obstacles like cholera, hostile Indians, inclement weather, and, of course, life-threatening diarrhea, the West was never as wild or adventurous as it was in The Oregon Trail.